We’ve all been there. You roll out of bed and the first thing on your mind is “How quickly can I get some coffee into my system?!” For me, it’s a quick run up to La Colombe. I think we all like the idea of throwing on Megadeth t-shirt and strutting down the street like Bobby Axelrod, but that look really only works when you run your own hedge fund. For the rest of us, we end up looking more like some frathouse schlub rolling up to the counter with sleep crust still in our eyes.

I’m on a personal mission to wear shirts with a little more structure whenever I feel like wearing a t-shirt. The added structure of a collar or open V help to frame my face better. This gives a greater sense of proportion balancing out my head and shoulders as well as highlighting my facial features.

Polo Shirt

Polo shirts are my personal choice to replace my t-shirts. They’re soft, comfortable, and classic. They also require minimal maintenance. Just wash and hang dry. My favorites are the Lacoste slim fits, but I also like the Brooks Brothers slim fit polos, which tend to be a little thicker than the Lacoste polos. The regulars fits for both Lacoste and Brooks Brothers are great as well for guys who might fall on the huskier side of the scale.

Henley Shirt

I’m going to be honest. I don’t wear henleys. At, 230 pounds, I’ve got a pretty big frame, and they’re just not for me. I think they work best on thinner guys and extremely fit guys. The lack of a collar works especially well for guys with thinner faces. However, the buttons and open V add that extra bit of structure that t-shirts lack. Buy adding this little but, the henley shirt definitely steps its game up from your basic T.

Popover Shirt

Popover shirts are what all dress shirts used to be. Many people attribute the popover to Gant in the 1960s, but in fact they are much older. Popover shirts were worn before the first full button up shirts were even invented, tracing their roots back to the tunics of the Renaissance. Today, popovers have become more casual options with button up shirts replacing them in formal dress wear. Popover shirts are a great way to break up your cycle utilizing their ideal blend of structural and relaxed style.

So my challenge to you is that the next time you are struggling to break the t-shirt rut, grab a polo, henley, or popover. Try a shirt with just bit more structure and notice the difference it makes in your personal style.